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Bisoctrizole

Bisoctrizole

Synopsis, Chemistry

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Also known as: 103597-45-1, Tinosorb m, Ultraviolet absorbent uv-360, Mbbt, Uv-360, Fat 75'634

Molecular Formula

C₄₁H₅₀N₆O₂

Molecular Weight

658.9 g/mol

InChI Key

FQUNFJULCYSSOP-UHFFFAOYSA-N

FDA UNII

8NT850T0YS

Bisoctrizole, or methylene bis-benzotriazolyl tetramethylbutylphenol, is a broad-spectrum organic UV filter that is marketed as Tinosorb M. It is a benzotriazole-based organic compound that absorbs, reflects, and scatters both UV-A and UV-B rays. Bisoctrizole is not approved by the FDA, but is approved in the EU and other parts of the world as a UV-filter in sunscreens, day care products and skin lightening products at a maximum concentration of 10%.

1 2D Structure

Bisoctrizole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(benzotriazol-2-yl)-6-[[3-(benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol

2.1.2 InChI

InChI=1S/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21-29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3

2.1.3 InChI Key

FQUNFJULCYSSOP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)CC(C)(C)C1=CC(=C(C(=C1)N2N=C3C=CC=CC3=N2)O)CC4=C(C(=CC(=C4)C(C)(C)CC(C)(C)C)N5N=C6C=CC=CC6=N5)O

2.2 Other Identifiers

2.2.1 UNII

8NT850T0YS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Methylene Bis-benzotriazolyl Tetramethylphenol

2. Tinosorb M

2.3.2 Depositor-Supplied Synonyms

1. 103597-45-1

2. Tinosorb M

3. Ultraviolet Absorbent Uv-360

4. Mbbt

5. Uv-360

6. Fat 75'634

7. Milestab-360

8. Tinuvin-360

9. Nsc-759873

10. 8nt850t0ys

11. 2-(benzotriazol-2-yl)-6-[[3-(benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol

12. 2,2'-methylenebis[6-(benzotriazol-2-yl)-4-tert-octylphenol]

13. Fat-75634

14. Ncgc00167544-01

15. 6,6'-methylenebis(2-(2h-benzo[d][1,2,3]triazol-2-yl)-4-(2-methylheptan-2-yl)phenol)

16. Phenol, 2,2'-methylenebis(6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-

17. Phenol, 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-

18. Bisoctrizole [usan]

19. 2,2'-methylenebis

20. Bisoctrizole (usp/inn)

21. Bisoctrizole [mi]

22. Bisoctrizole [inn]

23. Dsstox_cid_26703

24. Dsstox_rid_81837

25. Unii-8nt850t0ys

26. Dsstox_gsid_46703

27. Schembl39191

28. Bisoctrizole [mart.]

29. Ultraviolet Absorber Uv-360

30. Bisoctrizole [usp-rs]

31. Bisoctrizole [who-dd]

32. Bisoctrizole [usan:usp:inn]

33. Chembl2104957

34. Dtxsid2046703

35. Bisoctrizole, Analytical Standard

36. Chebi:135865

37. Hms3264f09

38. Pharmakon1600-01503866

39. Bcp29317

40. Hy-b0897

41. Bisoctrizole [usp Monograph]

42. Tox21_112541

43. Mfcd00192289

44. Nsc759873

45. S4551

46. Uv 360

47. Zinc11677911

48. Akos015895745

49. Db11262

50. Nsc 759873

51. Ncgc00167544-02

52. Cas-103597-45-1

53. Ft-0642535

54. M1259

55. A14939

56. D03249

57. Ec 403-800-1

58. Ab01563348_01

59. A800767

60. Sr-01000883719

61. Tinosorb M Pound>>ultraviolet Absorbent Uv-360

62. J-525148

63. Q4918369

64. Sr-01000883719-1

65. Bis-[2-hydroxy-5-t-octyl-3-(benzotriazol-2-yl)-phe

66. Bis-[2-hydroxy-5-t-octyl-3-(benzotriazol-2-yl)-phenyl) Methane

67. Bis[3-(benzotriazol-2-yl)-2-hydroxy-5-tert-octylphenyl]methane

68. Bisoctrizole, United States Pharmacopeia (usp) Reference Standard

69. Methylene Bis-benzotriazolyl Tetramethylbutylphenol [inci]

70. 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-yl-phenol]

71. 2,2'-methylenebis(6-(2-benzotriazolyl)-4-(1,1,3,3-tetramethylbutyl)phenol

72. 2,2'-methylenebis(6-(2-benzotriazolyl)-4-(1,1,3,3-tetramethylbutyl)phenol)

73. 2,2'-methylenebis(6-(2hbenzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]

74. 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 99%

75. Bisoctrizole, Pharmaceutical Secondary Standard; Certified Reference Material

76. 2-(2h-1,2,3-benzotriazol-2-yl)-6-{[3-(2h-1,2,3-benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl}-4-(2,4,4-trimethylpentan-2-yl)phenol

77. 3-(benzotriazol-2-yl)-2-[[2-(benzotriazol-2-yl)-6-hydroxy-4-(1,1,3,3-tetramethylbutyl)phenyl]methyl]-5-(1,1,3,3-tetramethylbutyl)phenol;2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]

78. 6,6'-bis(2h-1,2,3-benzotriazol-2-yl)-4,4'-bis(2,4,4-trimethylpentan-2-yl)- 2,2'-methylenebiphenol

79. Phenol, 2,2'-methylenebis(6-(2h-benzotrialzol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-

2.4 Create Date

2005-09-09

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₅₀N₆O₂
Molecular Weight	658.9 g/mol
XLogP3	12.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	10
Exact Mass	658.39952486 g/mol
Monoisotopic Mass	658.39952486 g/mol
Topological Polar Surface Area	102 Å²
Heavy Atom Count	49
Formal Charge	0
Complexity	989
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for use as a sunscreen agent in cosmetic products.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Under the conditions of _in vitro_ androgen competitive binding assay, bisoctrizole displayed no intrinsic androgenic, estrogenic, nor uterotrophic activity.

5.2 Absorption, Distribution and Excretion

Absorption

A rat and human dermal penetration study _in vitro_ indicates that bisoctrizole displays minimal absorption through the skin, with only about 0.01% and 0.06 % of the applied dose penetration through the human and rat skin membrane, respectively. Despite low dermal uptake, potential bioaccumulation after repeated skin applications cannot be excluded.

Route of Elimination